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Chapter 28 by Alostsoul Alostsoul

How does your session with Riley go?

It begins slow, and steady

“Welcome to your mistress’s domain.” Riley says with a giggle, sauntering along with you on the leash as she sweeps her arm acoss the room to draw your eye across her ‘domain’.

Her apartment is actually really nice looking, with you seeming to currently be standing in her living room, which connects right to the entrance. There you see a high end couch, and cushioned chair set, followed by artsy looking small table which sits on a sizable black carpet. The lay out of the room seems to revolves around a large flat screen TV hanging on the wall to right, the wall being a covered in layer of pure white paint. The floor is made up of bleached white wood which is polished so well it practically shimmers from any form of light. Which speaking of light to the left you see the sunlight pouring through a large clear glass wall which is possible as Riley’s room borders the outside of the building.

Before you can finish looking over the room though you hear a noise which startles you. You quickly dart you head around the room confused till you detect that the source of the sound is coming from above.

“Ruff, ruff, ruff, ruff!!”

There you see a rowdy chiwawa barking down at you from the second floor that you just now noticed. He glares at you with aggressive, and suspicion as he yipes out his most ferocious yaps, and growls he can muster. The small cainie looks almost ready for a fight, eager to chase you out of his territory. The only thing preventing him seeing to be a black wood spiraling stair case which seems much to steep for him to climb down with out falling.

“Little clam down, bad boy no yapping!” Riley scolds the dog in a snippy tone as she takes off her jean jacket.

“Hehe I think he’s mad because you’ve stolen his stuff.” Riley grins in amusement at you as she looks at the collar round your neck.

You put a hand up to the tag on the collar looking down the name engraved just to confirm for yourself.

The verification that this is indeed the property of the chiwaw hits you wish a new rush of embarrassment, and twitch from your caged cock as a result. You can’t help but draw a parallel between your current status, and the barking puppy displeased by your presence. Like him, any attempt at hostilely, or endeavor to seem to tough would probably be seen as humorous or even cute by Riley, as she has gotten you naked, chastise, and leashed before her so easily. Truly any attempt to establish dominance now would only accentuate the inverse in your position.

“Well I mean you did give me this stuff.” You respond to Riley shifting the blame for this perceived slight on to her.

“Ha, do you really want to give me such a sarcastic response, like shouldn’t I be able to punish you for mouthing off?” Riley curvles the right part of her mouth into a half smile, though you can’t tell if her pure joking or subtlety asking you for permission.

You feel your heart skip a beat with just the mention of punishment. Your cock again is reminded of its prison as you think back to your time with Harper. The sting, it hurt yet it also turned you on, and based on the reaction your having now has at least particularly changed how your relationship with pain. You feel bashful, part of you wanting to out right ask for a punishment, yet part of you also still embarrassed for having such thoughts let alone saying them out loud.

“If that’s what you want to do.” You shrug attempting to seem casual about such suggestion, as you take a happy medium with neither asking for, nor rejecting the idea.

“I see well I’ll keep that in mind, but I’m not going to jump the gun on something like that just yet, I’m a benevolent master so I’ll save the punishment for when you do something really bad.” Riley says, doing a curtsy just to show how much of ‘kind gentle lady’ she is.

“Ruff ruff ruff ruff ruff!!”

Little keeps yapping his head off at you as he stares down at you between the railings of the top floor, even though Riley had scolded him.

“Ugh he’s not going to stop till I put him in his cage he’ll warm up to you eventually but that’s gonna take a while he hates strangers.” Riley rolls her eyes at dog as he continues with noisy moral outrage.

“Here you can just take a seat in the living room while I put him away, I assume you don’t need me to lead you over their.” Riley giggles as she hands you the lead of your on leash.

“Yeah right no problem.”

Tracy then walks off climbing up the spiral stair case so that she can deal with her dog.
With the briefest of normalcy in that interaction you forget your situation for just a split second, it felt like you were just a guest at the house of a new friend, the familiar curiosity, and excitement of exploring a new person’s house taking you back to the days when you would sleep over with school mates. Though that feeling quickly dissipates as the weight of the leash in your hand brings you back to your current moment in reality. You wrap an arm around yourself, the temperature in the room a bit more chilly then it was out in the hallway. This causes you to feel your nakedness all the more, your skin tingling a slightly form the enhanced sensitive of the cool air. Deciding to get off your feet, you take a seat on the near by couch. The fabric feels so good against your bare skin, that you even considering grinding your balls agains the seat cushion as you sit to edge out just a little bit of pleasure. Yet you know that’s only going to result in you getting hard in your cage, and potentially leaking on Riley’s nice furniture so you decided against doing that, opting to just sit, and look around the room some more while Tracy takes care of her dog. Now that you’re taking a better look at the room you come to the conclusion that the band must bringing in nice chuck of change. Not only is this apartment it’s self kind of fancy what with their being a manned lobby tipping you off to that, but Tracy also a seems a few expensive art piece decorating the room. Or when you believe they look expensive you can’t really tell your not an art appraiser.

You then turn your head as you hear the sounds of foots steps coming down the revolving stairs.

“Okay I put him in his cage so he won’t bother us.” Tracy says as you see here reach the bottom step, her seeming to have removed her jacket, sun glasses, and bandana while she was upstairs.

Trotting up to the couch she suddenly stops about a foot away at you, and narrows her eyes at you. Not in a angry way, but more so a suspicious or thinking way.

“Is there something wrong?” You ask wondering what’s up.

“Hmmmm now this doesn’t seem right, I feel like you should be kneeling rather then sitting if your going to wait for me.” Says Riley as she thoughtfully taps a finger to her chin.

Your cock throbs again, and you swiftly slide from the couch to kneel down on the carpet. Now looking at her from your lower position, you see Riley with more of an air of authority then before. You can feel your heart start to quicken at the thought of being dominated again. Of being submissive to her.

“Woah I was just kind of thinking out loud you don’t actually have to kneel down like that, I don’t want you to be rough on your knees.” Riley speaks with genuine surprise at you instantly obeying her suggestion like that.

“O-oh umm no I’m fine mistress the carpet is a good enough cushion. You reply feeling a sense of awkwardness as Riley’s caught off guard reaction to your eagerness makes you feel a little silly.

“Huh okay then if you want to kneel for me then kneel for me.” Riley says trying to dissipate some of the awkwardness with a supportive smile.

You give her a thankful look in return, and watch as she plops down on the couch in front of you.

“Now I know your obvious pent up, but is there anything you want before we start, food, drink anything at all?” Riley offers as she sits up, and runs her eye over your naked body.

She’s seen you naked before at the part, but this time there’s something different. The position your in, kneeling down in front of her with that chastity cage, it make you look quite cute, cuter then Riley previously thought of you as, which was already pretty cute. The birds eyes view she has of you, the way your hands are laid neatly on your knees. It makes Tracy’s chest swell with desire. Two parts of mind tugging in different directions on what she wants to do to you. One half wants to tease you, to bind you, grope you, fondle you. Truthfully rather mild stuff in terms of bdsm that a dominate might, but it’s reflective of Riley’s personality as she’s the self admitted ‘normie’ the band. The other half of her cravings is evens more vanilla though, as he other half wants to pamper you. Cuddle you, kiss you, hug, all that lovey dovey stuff that would melt even the most stolid of men’s hearts into a puddle of warm fuzziness. Still what ever method of attack Riley chooses in this encounter, it’s clear to her you’ve awoken something with in her.

“Well it’s a little cold?” You say posing the words as almost a question as to not seem to overly concerned with such a minor thing.

“Right I’ll adjust the temperature then, you just hold that poise for me like a good boy.” Riley giggles, patting you on the head as she walks past you to adjust the thermostat.

The words good boy reverberate in your ears the vibrations of sound sending a shiver down your spine all the way to the tip of your cock. You feel yourself slipping into that submissive state where you just want to listen, and obey. Mind content to take whatever Riley had in store for you. Relaxing your breathing you think back to when you were in sub space with Harper, and try your best to replicate that feeling. It’s hard though, and you realize you can’t get there yourself, you need to be led there by someone.

“Okay I turned the temp down a few notches, though I left it kind of cool as my moneys on you natural getting hotter in a moment.” Riley says sitting back on the couch swinging one leg over the other to now sit cross legged in front of you, one of her legs bouncing up, and down casually.

“Alright, oh I almost forgot we need a safe word hmmmm, let’s go with I don’t know velvet yeah velvet sounds good, now what is the safe word?” Riley asks you.

“It’s violet mistress.” You say repeating the word back to Riley.

“Good just wanted to make sure you said it out loud, helps so that you don’t forget in the moment ya know.”

Riley then pats the seat on the couch next to her.

“Now with every thing sorted out why don’t you come take a seat next to me.” Riley’s voice now has a tangible hint of lust in her tone as she talks.

It’s not obvious, she’s still has a very friendly and causal demeanor, but you can’t tell theirs the tell tale signs of creeping arousal. Knowing this causes your heart to speed up as you too become a little excited, though it’s probably pretty apparent as your increased speed of your rising, and falling chest is easy to see with you naked. Obeying Riley you sit on the couch next to her, the two of you facing each other with only about half a foot of distance between you both. Being so close now you can smell the sent that mango perfume again.

“I.... know that your pent up right now, but do you mind if we go slow I kind of want to spoil you right now.” Riley asks leaning her face closer to yours, her pretty features keeping your eyes locked on to her face.

You cringe at the request balls swollen an aching, but you can’t bring yourself to say no. Maybe it’s because of how friendly Riley has been to you, treating you like a good friend despite this only being your second meeting. Or maybe it’s because your just too horny and submissive right now to deny a sexy girl.

“You can do what you want mistress.” Either way you selflessly whisper permission for Riley to set the pace rather then you greedily insisting on her making you cum now.

“Thanks Doug.” Riley says a great full expression on her face.

She then simultaneously runs her left hand from couch on to your right thigh, as then closes her eyes, and leans her head forward. As her finger tips glide across your skin you close your eyes to, and mimicking Riley meet her half way for a kiss. You taste strawberry like you did before in the car as your lips make contact, her digits dancing along your smooth hairless leg as she indulges in the taste of you. Riley kisses you gently, softly, giving you slow yet short pecks on the lips, each other’s hot breath mixing with one another as you break apart to breathe. Another hand of Riley’s then joins the fray her right hand looping around your left side to gradually surf her hand up your back.

It’s like she studying your body through her hands, feeling the blood pump through you. You rhythmic breathe in and, out at steady pace. Your muscles relax and flex unconsciously, and natural. Her right hand feeling like it’s trying nap out your anatomy just by touch, it running from your spine, the back of your neck, all the way down to your ribs, and your hips. Meanwhile her left rubs all over your up your right thigh squeeze it ever so slightly in different places as if to compare the softens and firmness in each location. The experiences is strange almost feeling like your being examined by a doctor or scientist but in a good way. Not with a cold and clinical lack of emotion but, a hearty fascination, and curiosity. Like even inch of your body is some sort of wondrous new discovery that needed to be studied.

The comparison isn’t that too far off though, as you’ve sort of spurred something with in Riley. As a he suddenly has the compulsion to really appreciate ever part of this intimate moment. To focus on every detail of the touch, and taste of you as she feels you up, and kisses you. Of course Riley did always appreciate a little fore play when it came to hooking up with some one, even some of the groupies she took back stage with her were surprised, that she would sometimes indulge in making out, or cuddling before she fucked them. Certainly not what they expect to some metal band chick who preformed on stage with her cock out. Even still what Riley is feeling now is different then just some foreplay. She is legit enjoying just showing you affection, and feeling your body react to said affection. She can’t explain why though...

“Ah hey let’s take this up to bed room k?” Riley then says her breathing seeming slightly elevated as she gives you another quick kiss on the lips.

“If that’s what you want mistress....” You reply cock now pushing at the walls of your cage due to all the touching, and kissing.

Riley then stands up, taking hold of the lead on your leash she gives a gently tug for you to follow. You obey standing up as well, and trotting a few feet behind as she leads you pasted the living room, and into a small hallway. There your led to a black wood door at the end of the hallway which Riley opens, as she’s gives you another tug on the leash this time a little harder, clearly showing some increased eagerness on her part. Her bedroom is very stylish, and fancy looking. A modern looking sleek black wood dresser against the wall on the left hand side, with a small blue tooth stereo. An desk with a lit up LAD computer, and monitor on the right. In the center of the room is a large king black wood king sized bed, which has a large zebra patterned blanket on top. Next to the bed is a small nightstand with a stylized lamb on top of it. The floor is made up of a fuzzy green carpet, while the walls are painted a cool sky blue with some more artsy paintings hang there as well just like the living room.

“Lay down on the bed there’s a few things I want to get real quick.” Riley says throwing the end of leash to you which you just barely catch.

You obey taking a seat on the bed, and crawling over to the top. Though you have trouble finding a position to lay down in that doesn’t make you feel awkward. So small you are compared to the bed, and with you naked and all, it just make you feel like a meek, helpless maiden awaiting a ravaging by their lover. Which yeah is mostly true, but come on it still makes you feel just a little bit embarrassed! Try as you might, ever pose you try still leaves you with that peculiar feeling yet the best you can come up with is laying on your side in a sort of s shape hand on your hip, while the other hides your caged cock. Sure you still look pretty helpless, but it’s better then looking so willing to be fucked. You do have some dignity after all! Despite the uh, dog collar round your neck...

Just then you hear Riley shut the drawer of the dresser she was rummaging through, she seems to be holding a bunch of stuff with both of her arms yet you can’t see it from your position in the room. Then strangely Riley walks backward toward you with her back still turned to you. Once she then bumps into the bed she drops the hand fulls of what every she has right at the foot of the bed.

“Ahh ahh ahh no peeking Dougie, I got a few things I want to keep secret hehe.” Riley scolds you, hands on her hips as she sees you try to crawl over to the end of the bed to see what all that stuff she has is.

That makes you worry a little thinking back to Harper’s cruel whip, and your complicated relation you had with it. Yet, it also kinda of excites you, your mind starting to think up possibilities of what things the strawberry blonde has in store for you.

“So now let me just get the atmosphere right in here.” Riley says as she trots over to the night stand by the bed.

There she picks up a small remote that you didn’t notice before, and taps a few buttons. The lights of the bed room then suddenly dim, and the color changes to a warm wine red. Then Riley pulls out her phone, and makes a few taps on that as well. The stereo on the dresser then springs to life, and begins playing a relaxing lo-if jam from the speakers.

“There we go.” Riley then says
kicking off her shoes, and heading back to the end of the bed again.

She then grabs something from the floor, and hiding it behind her back slinks back around the side of the bed making sure to keep the object hidden from your field of vision. She then takes a set on the end of the left side of the mattress, and pats her lap as she gives you a small smirk. You gulp, presuming that you know what kind of object she has if she wants you to lay over your lap. Even with the impending threat of pain though you dick presses against its pink plastic prison, you masochist side salivating with the thought of some delicious pain. Slowly your crawl over to Riley on the bed on hands and knees. You still can’t see what she has in her hand, and her way she is facing has it so that your aren’t looking towards the end of the bed so you don’t even get a chance to get a better look at the other items she has.

There is sort of a strange calm in you as you lay your self over her lap though. An acceptance of your fate, a submissive resolve to face what ever Riley is going to do you with out resistance. As your bare skin touches her jeans, and you lay your full weight I’ve your thighs you just exhale deeply letting it all go.

“You remember your say word?” Riley asks you as she gently places a comforting hand on your back.

Rubbing softly between your shoulder blades, and small of your back in attempt to soothe you even further into a feeling of clam.

“It’s velvet mistress...” You trail off as you shiver under Riley’s touch, not because her hands are cold, but because her touch tantalizes you, makes so fucking ready.

“Glad you remembered, don’t forget to use it if you need to trust me I won’t be offended.” Riley jokes, as her hands begin to move.

You close your eyes, thinking this must be it, as you imagine her raising some paddle or crop, or flogger high above her head. Only you then hear something strange. You hear the sound of a cap snapping opening. Deciding to open your eyes, and crane your neck to the right you finally catch a glimpse of what Riley is holding out of the corner of your eye.

“Oh-h.” You can’t help but, blurt your surprise as you see Riley squirting some lube from a bottle into her hand.

“Something wrong Doug?” Riley asks picking up on the surprise on your face.

“Oh n-no nothing I just thought...” You trail off feeling a bit foolish you were so sure that you were about to receive a spanking.

Riley stops what’s she’s doing, sensing the awkwardness you feel she assumes she’s done something wrong. Riley narrows her eyes trying to figure what misstep she made here. Then her expression turns to one of amusement as she seems to figure what’s going on.

“Man, Harper really did a number on you, girl really flipped a switch in you huh.” Riley laughs knowing that your assumption of pain had to have been ingrained in you by her sadistic fellow band mate.

You feel a little bit of redness on your cheeks, your blatant misgivings about the situation leaving you a little embarrassed. Argh your sure probably thinks your some pain hungry slut to Riley now! However a friendly pat on your head from her tells you different.

“Don’t worry Doug I’m not as harsh as Harper when it comes to this stuff, well unless you want me to be.” Riley coos tracing a finger down the back of your neck.

You shiver.

“Only if that’s what you want mistress.” You reply as you feel your cock again straining.

“Then forgot about pain for now, I know, I know, I’m a coward but I don’t really like hurting people gives me the ick.” Says Riley sticking out her tongue and making a face.

You then hear her squirt some more lube from the bottle she has into her hands. Riley then rubs her hand together making sure they are fully coated in a lot of lube. You jump a little as the cold liquid touches your skin, Riley now placing a hand on one of your ass cheeks. You know were this is going as she spreads your cheeks apart with her pointer finger, and thumb her appearing to be examining you twitching hole. You then feel her thumb position itself right up against the ring of your backdoor.

“I’m going to push in now, just relax and breathe out for me okay.” Riley commands in soft, but firm tone.

“Yes mistress....” You reply in whisper your cock starting to leak on to Riley’s jeans, as arousal starts to really build with in you.

As you then breath out deeply like she told you to , Riley then pushes forward. You feel a brief sensation of pressure as her thumb makes her way past the rim of your ass hole, followed by a sense of relief as you then feel it slip inside you. With her thumb being so small compared to other things that you have had inside your ass you don’t really have a feeling of fullness, though does feel satisfying to be able to clench your anus around something no matter how small it is. Riley proceeds to then push her thumb deeper inside of you, swoly crawling inch by inch, you involuntarily felex, and un-flex around her finger till she’s all the way to the third knuckle. Even with such a small little thing inside of you, you can’t help but grind your crotch against Riley’s lap. Even with your cock unable to feel the stimulation the grinding massages your balls, making them tingle, and ever so slightly moves Riley’s thumb back, and forth in your butt.

“Well now aren’t you eager I haven’t even started yet, and your already rocking your hips, am I that good.” Riley says smiling a hint of lighted hearted sarcasm in her voice as she looks down at you.

“Sorry mistress I-I got to eager.” You apologize immediately ceasing any movement.

Tension fills you as you freeze up, and lock all yo muscles in place. You silence any involuntary movements besides your breathing, holding yourself still like statue. Or more accurately a doll, a doll for Riley to do what ever she wants to it.
You wish to keep going, but that submissive part of you screams for your obedience, and self sacrifice. It making your head bubble, and heart beat fast as the action of submission turns you on so much. The casting aside of your own pleasure, making you even more horny, and needy. Sending you to that place which makes you drip, and throb, and leak.

“Hey you can chill a little, I get you got a submissive streak, and I’m sort of the dom here, but you don’t have to focus so much on making sure you obey me just let me take the lead okay.” Riley speaks in a cheery tone that fills you with warmth, that friendly personality of hers really shine though, even with her finger inside of you.

With that Riley then starts to move her thumb back, and forth inside of you, and as she’s given you permission to do so, you rock your hips again to meet her finger. It’s a small buzz of pleasure to be sure with her only using one of her digits, but it succeeds in partly receding some of the unbearable horniness you have been feeling. Then Riley curls her finger, and lightly presses your prostate. You a spark of electricity hits you. Your breathe is caught in your throat as you mouth opens wide. A little ‘Ah’ of a moan then escapes you, your cock spilling another tear of pleasure from its head. Riley bites her lip, as a small ‘Ah’ of her own escapes as well. It’s amazing, adorable, sexy, beautiful! All these words come to mind as she again presses your prostate, and watches your reaction. She can see ever detail of you, ever fiber of your begin. Ever twitch your body does, ever sound your voice makes. It is an experience nothing else in life can even come close to providing.

Riley starts to move her thumb, back and forth inside of you a bit faster now, pulling back all the way till she’s almost out of you, before plunging her finger all the way back in. With ever thrust she’s gives your special button a press, and to her delight you make more noises, more movements of your body. Just watching the process makes Riley’s own cock start to stir, and the knowledge that she is the one doing it turns her on so much. One would be right it saying it’s her outgoing friendly nature that makes her love this. Peoples emotions, and reactions she loves seeing them, and seeing such intimate ones is such treat for her. It’s why she’s teasing you right now, why she was touching you, and tasting you with such an intense focus before.

“Ahhh!” With one particular deep press against a certain spot on your prostate you can’t help but completely vocalize an almost girl, pleasured moan.

“There we go that’s the spot...” Riley whispers seemingly to her self.

She then press at the same sport not even bothering to thrust with her finger, getting tunnel vision as she just wants to hear you moan like that again.

“Ahhhh!”

“Ahhhh!”

“Ahhhhhhh!”

“Ahhhhhhhhh!”

“Ahhhhhhhhhhh!”

“AHHHH!!”

You moan louder, and louder, leaking more from the head of your cock. The pre cum getting smeared around on Riley’s lap, as you keep rubbing yourself across her legs, your sack tingling as you are practically humping yourself on Riley like a horny dog. Pretty appropriate as your still wearing that dog collar, and leash.

“AHHHHH!”

“AHHHHHH!

“AHHH!”

“Ahhh!”

“Ahhh!”

“Ahh!”

“Ah!”

“Ah!”

Riley’s fingering then starts to get slowly, and softer the pleasure she’s giving you deceasing with each press now. Till finally she stops all together, and pulls her thumb out of your ass.

“Uhhhhhhhhhh....” You groan in misery craving the now missing stimulation, the finger that seemed like so little compared to what you’ve taken before now some how making you feel so empty.

“Mistresss pleaseeee...” You whimper still humping against Riley trying desperately to make up for the new lack sensation.

Riley just looks down at you with eyes ablaze with passion. Your begging, and twitching making her cock swell more. Your just so goddam cute. The desperation, and neediness making you move in such wondrous ways. Your voice speaking with such beautiful emotion is practically music to her ears. Riley isn’t heartless though as she places a hand on your blonde head, helping you calm back down as she strokes your hair.

“Shhhh shhhhh calm down, I know, I know, we’re just getting started though I believe in you.” Riley apologizes, pangs of guilt prickling her for teasing you like that.

Not enough for her to regret what she did, but enough for her to be empathy to your plight. She then takes you in her arms, turning you around on your back to face her she lifts you up, and embraces you in a hug. She cuddle you for a minute or two feeling your body recover from the frustration, savoring every detail from you. You grateful accept the sympathy in her arms. Even though she’s the one whose denied you even the beginning of building pleasure, your submissiveness, and desire for some sort of comfort has you nuzzle into her chest like a crying child, despite her being the one toying with you.

After a few more minutes or hugging, you start to calm, your cock as well. It now deflating to a half chub rather then at full erect.

“Okay, okay, there, there.” You smiles giving you a pat on the back.

She then stands up, and you almost want to cling onto her, but you **** yourself to reliant.

“I’m going to get somethings to spice this up a bit Doug, do me a favor and close your eyes, I want to be a surprise.” She says grinning at you as she gives a wink.

“Yea mistress.” You nod now calm again.

Closing your ears you perk up your ears as you listen to Riley walk over to the end of the bed. You hear her rummaging through the pile of items, and you speculate on what she could possible be grabbing.

What does Riley grab?

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